Fenofibrate

Base Information

• Chemical Name: Fenofibrate
• CAS No.: 49562-28-9
• Molecular Formula: C20H21ClO4
• Molecular Weight: 360.837
• Hs Code.: 2932999099
• European Community (EC) Number: 256-376-3
• NSC Number: 757822,281319
• UNII: U202363UOS
• DSSTox Substance ID: DTXSID2029874
• Nikkaji Number: J10.021H
• Wikipedia: Fenofibrate
• Wikidata: Q419724
• NCI Thesaurus Code: C29047
• RXCUI: 8703
• Pharos Ligand ID: 7Z7V63X5PCKY
• Metabolomics Workbench ID: 43281
• ChEMBL ID: CHEMBL672
• Mol file: 49562-28-9.mol

Synonyms:Antara Micronized Procetofen;Apo Feno Micro;Apo Fenofibrate;Apo-Feno-Micro;Apo-Fenofibrate;AZU, Fenofibrat;CiL;Controlip;Debat, Fénofibrate;durafenat;Fénofibrate Debat;Fénofibrate MSD;Fenobeta;Fenofanton;Fenofibrat AbZ;Fenofibrat AL;Fenofibrat AZU;Fenofibrat FPh;Fenofibrat Heumann;Fenofibrat Hexal;Fenofibrat ratiopharm;Fenofibrat Stada;fenofibrat von ct;Fenofibrat-ratiopharm;Fenofibrate;Gen Fenofibrate;Gen-Fenofibrate;Heumann, Fenofibrat;Hexal, Fenofibrat;LF 178;LF-178;LF178;Lipanthyl;Lipantil;Liparison;Lipidil;Lipidil Ter;Lipidil-Ter;Livesan;Lofibra;Micronized Procetofen, Antara;MTW Fenofibrat;MTW-Fenofibrat;Normalip;Novo Fenofibrate;Novo-Fenofibrate;Nu Fenofibrate;Nu-Fenofibrate;Phenofibrate;PMS Fenofibrate Micro;PMS-Fenofibrate Micro;Procetofen;Procetofen, Antara Micronized;Procetofene;Secalip;Stada, Fenofibrat;Supralip;Tricor

Chemical Property of Fenofibrate

Chemical Property:

• Appearance/Colour: Crystalline solid
• Melting Point: 80-81 °C
• Boiling Point: 469.8 °C at 760 mmHg
• Flash Point: 165.4 °C
• PSA: 52.60000
• Density: 1.177 g/cm³
• LogP: 4.68000
• Storage Temp.: Store at RT
• Solubility.: Practically insoluble in water, very soluble in methylene chloride, slightly soluble in ethanol (96 per cent)
• Water Solubility.: 0.8mg/L(25 oC)
• XLogP3: 5.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 7
• Exact Mass: 360.1128368
• Heavy Atom Count: 25
• Complexity: 458

Purity/Quality:

99%, ^*data from raw suppliers

Fenofibrate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn, Xi
• Hazard Codes: Xn,Xi
• Statements: 22-36/37/38
• Safety Statements: 36-26-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Drug Classes: Antilipemic Agents
• Canonical SMILES: CC(C)OC(=O)C(C)(C)OC1=CC=C(C=C1)C(=O)C2=CC=C(C=C2)Cl
• Recent ClinicalTrials: An Efficacy and Safety Study of Alirocumab in Children and Adolescents With Heterozygous Familial Hypercholesterolemia
• Recent EU Clinical Trials: Fenofibrate as a Metabolic Intervention for Coronavirus Disease 2019 (COVID-19): A randomized controlled trial (FERMIN trial)
• Recent NIPH Clinical Trials: Randomized controlled trial of pemafibrate and fenofibrate for NAFLD with hypertriglyceridemia
• Description: Fenofibrate is a medication approved by the FDA for the treatment of hyperlipidemia with elevated triglycerides (TGs) or mixed hyperlipidemia with elevated TGs and reduced high-density lipoprotein cholesterol (HDL-C) levels.^[1]
• Uses: Fenofibrate is primarily used to treat hyperlipidemia and related cardiovascular risk factors. It also exhibits pleiotropic effects such as anti-inflammatory, antioxidant, and antiviral characteristics. Fenofibrate was first synthesized in 1974 and has been used in medicine since 1975. It has since become a key medication for the management of hyperlipidemia and related conditions. ^[2]
• Mechanism of Action: Fenofibrate is a phenoxy-isobutyric acid derivative that is metabolized to fenofibric acid, an active metabolite. It's chemical structure enables activation of the peroxisome proliferator-activated receptor alpha (PPAR-α), leading to modulation of various genes involved in lipid metabolism, fatty acid oxidation, and inflammation. This mechanism helps lower blood lipid levels and reduce inflammation.^[1],[2]
• Potential uses: Fenofibrate has been studied for its potential therapeutic efficacy in NAFLD, showing antioxidant, anti-inflammatory, and antifibrotic activity.^[3]
• References: [1] Anti-inflammatory role of fenofibrate in treating diseases; DOI 10.17305/bb.2022.8534; [2] Fenofibrate for COVID-19 and related complications as an approach to improve treatment outcomes: the missed key for Holy Grail; DOI 10.1007/s00011-022-01615-w; [3] Impact of fenofibrate on NAFLD/NASH: A genetic perspective; DOI 10.1016/j.drudis.2022.05.007

Technology Process of Fenofibrate

There total 42 articles about Fenofibrate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 94.9%

fenofibric acid (42017-89-0) + isopropyl bromide (75-26-3) → fenofibrate (49562-28-9)

Guidance literature:

fenofibric acid; With potassium carbonate; In Isopropyl acetate; dimethyl sulfoxide; at 20 - 90 ℃; for 0.75h; Industry scale; Inert atmosphere;

isopropyl bromide; In Isopropyl acetate; dimethyl sulfoxide; at 80 - 95 ℃; for 5.83333h;

Reference yield: 91.0%

isopropyl 2-(4-(1-(4-chlorophenyl)-2-methoxyvinyl)phenoxy)-2-methylpropanoate → fenofibrate (49562-28-9)

Guidance literature:

With tert.-butylhydroperoxide; copper (II) carbonate hydroxide; TPGS-750-M; In water; at 20 ℃; Green chemistry;

DOI:10.1021/acs.orglett.8b01883

Reference yield: 90.0%

isopropyl 2-bromo-2?methylpropanoate (51368-55-9) + 4-chloro-4'-hydroxybenzophenone (42019-78-3) → fenofibrate (49562-28-9)

Guidance literature:

With potassium hydrogencarbonate; In isopropyl alcohol; for 48h; Reflux;

DOI:10.1021/jacs.6b13113

upstream raw materials:

fenofibric acid

isopropyl alcohol

chloroform

4-chloro-4'-hydroxybenzophenone

Downstream raw materials:

fenirofibrate

isopropyl 2-(4-((4-chlorophenyl)(hydroxyimino)methyl)phenoxy)-2-methylpropanoate

isopropyl 2-(4-(4-hydroxybenzoyl)phenoxy)-2-methylpropanoate

2-[4-(4-Fluoro-benzoyl)-phenoxy]-2-methyl-propionic acid isopropyl ester

Refernces

• 1、 Zhang, Yilan,Yue, Xiaoguang,Liang, Chenfeng,Zhao, Jianming,Yu, Wenbo,Zhang, Pengfei. "Photo-induced oxidative cleavage of C-C double bonds of olefins in water". supporting information. . Retrieved 2021/08/27.
• 2、 -. "Aryl aldiketone and synthesis method thereof". Paragraph 0034. . Retrieved 2021/09/26.